Triethylamine → HCID 53241215, compound

HRID 527734Notes

Reaction equation

HRID 527734 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[NH2:19])=[CH:12][CH:11]=2)=[CH:5][C:4]=1[O:23][CH3:24])#[N:2].C(N(CC)CC)C.Cl[C:33]([O:36]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl>C(Cl)Cl>[CH3:21][C:18]1([CH3:20])[C:17](=[O:22])[N:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([O:23][CH3:24])[CH:5]=3)=[CH:15][CH:14]=2)[C:33](=[O:36])[NH:19]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 67235521HCID 67235521, compound

Product 1

HCID 53241215HCID 53241215, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

N1-(4-{[4-cyano-3-(methyloxy)phenyl]oxy}phenyl)-2-methylalaninamide (77.0 mg) was dissolved in DCM (10 mL). Triethylamine (0.218 mL, 1.57 mmol) was added and the obtained mixture was cooled at 0° C. Bis(trichloromethyl)carbonate (68.1 mg, 0.22 mmol) was dissolved in 5 mL of DCM and the obtained solution was added dropwise to the reaction mixture. The reaction mixture was stirred at 0° C. After 15 min, the reaction mixture was evaporated in vacuo to obtain the crude product that was purified by silica gel chromatography (from 100:0 to 50:50 Cyclohexane/EtOAc in 10 CV; then 50:50 Cyclohexane/EtOAc for 10 CV) to obtain 65.1 mg of the title compound as a white solid.

Workup

  1. additionthe obtained solution was added dropwise to the reaction mixture
  2. customthe reaction mixture was evaporated in vacuo
  3. customto obtain the crude product that
  4. customwas purified by silica gel chromatography (from 100:0 to 50:50 Cyclohexane/EtOAc in 10 CV

Sources & evidence

ORD record
ord-06979c4a4782498e8fceb7355b01278f
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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